N-bromobutanimide → 4-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzene

HRID 406348Notes

Reaction equation

HRID 406348 reaction equation
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:20])=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:20][Br:1])=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27756354-Methyl-3-(trifluoromethyl)bromobenzene

Product 1

HCID 534180314-Bromo-1-(bromomethyl)-2-(trifluoromethyl)benzeneYield 83.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (2.6 g) and 2,2′-azobis(isobutyronitrile) (35 mg) were added to a solution of 5-bromo-2-methylbenzotrifluoride (CAS #86845-27-4, 3.5 g) in carbon tetrachloride (35 mL), and the mixture was heated under reflux for five hours. The reaction solution was ice-cooled and then the insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Wakogel C-200; elution solvent: heptane) to obtain 3.86 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for five hours
  3. temperaturecooled
  4. customthe insoluble matter was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (carrier: Wakogel C-200; elution solvent: heptane)

Sources & evidence

ORD record
ord-2461f1cc56e645a1b2fbc5ea9b17090b
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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